CN105646761A - Preparation method of mesoporous polymer nanoparticles - Google Patents
Preparation method of mesoporous polymer nanoparticles Download PDFInfo
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- CN105646761A CN105646761A CN201610009434.7A CN201610009434A CN105646761A CN 105646761 A CN105646761 A CN 105646761A CN 201610009434 A CN201610009434 A CN 201610009434A CN 105646761 A CN105646761 A CN 105646761A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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Abstract
The invention relates to a preparation method of mesoporous polymer nanoparticles. The invention is technically characterized in that the preparation method comprises the following steps: by using styrene monomers and (methyl) acrylic acid (acrylate) and other monomers as comonomers, carrying out one-step soap-free emulsion controlled polymerization reaction in the presence of a control agent and an initiator to prepare the polymer nanoparticles, and sufficiently cleaning the polymer nanoparticles with water to remove the unreacted monomers, control agent and initiator, thereby obtaining the mesoporous polymer nanoparticles. The preparation method of the mesoporous polymer nanoparticles does not need any template, pore-forming agent or emulsifier, and only needs one-step simple polymerization reaction. The prepared mesoporous polymer nanoparticles have wide application prospects in the fields of gas storage and separation materials, carriers of drugs and bioactive materials, catalysts and catalyst supports, nano reactors, photon crystals, sensors and the like.
Description
Technical field
The present invention relates to the preparation method of a kind of polymer nano-particle, it is specifically related to the comonomers such as styrene monomer and (methyl) vinylformic acid (ester) and be polymerized the obtained polymer nano-particle containing meso-hole structure by a step soap-free emulsion control.
Background technology
Polymer nano-particle containing meso-hole structure is because of its higher specific surface area, varied and be easy to carry out the composition of chemically modified modification, regulatable aperture and pore structure and the field such as the carrier of the atmosphere storage that is widely used in, parting material, medicine and biological active materials, catalysis and support of the catalyst, nano-reactor, photonic crystal, sensor.
The preparation method of current mesoporous polymer nanoparticle mainly comprises template port-creating method, pore-creating agent port-creating method, multiple emulsion port-creating method etc. Wherein template port-creating method utilizes the silicon-dioxide prepared in advance, manganous carbonate, Z 250, gold, polymer nano-particle etc. to be template particles, outside template particles by graft polymerization, precipitation polymerization etc. coated on polymkeric substance, utilize acid, alkaline solution or organic solvent etc. template particles to be removed subsequently, obtain mesoporous polymer nanoparticle. Pore-creating agent port-creating method is taking Small molecule organic solvents, oligopolymer, segmented copolymer etc. as pore-creating agent, prepare in polymerization or self-assembly in the process of mesoporous polymer nanoparticle and it is separated with the polymkeric substance forming nanoparticle, pore-creating agent plays the effect of occupy-place in phase separation, removes pore-creating agent and obtain mesoporous polymer nanoparticle after being separated. And multiple emulsion pore-creating rule is a kind of soft template method not using template particles and pore-creating agent, the method adds tensio-active agent in polymerization system and forms the stable solvent phase of emulsifying agent by emulsifying effect in inside nanoparticles, after being polymerized can directly by solvent mutually in solvent extraction out obtain mesoporous polymer nanoparticle.
By the description to existing three kinds of methods preparing mesoporous polymer nanoparticle, template is a kind of method needing multistage processes, namely need first to prepare template particles, the last means removal that template particles utilizes various dissolving etching again, therefore makes this kind of method steps loaded down with trivial details and uneconomical;Pore-creating agent port-creating method needs additionally to add organic solvent or polymkeric substance in system, organic solvent and extract and make the method not only be unfavorable for environment protection as the organic solvent of the polymkeric substance of pore-creating agent, and adding of these pore-creating agents makes polymerization system become complicated, wayward; Although multiple emulsion port-creating method can avoid the use of organic solvent, but emulsifying agent must be added in system to form multiple emulsion, and emulsifying agent is difficult to remove from mesoporous polymer nanoparticle in subsequent processes, the emulsifying agent of residual seriously affect mesoporous polymer nanoparticle being separated, the carrier of medicine and biological active materials, application performance when catalysis and the field such as support of the catalyst and sensing use. At present, there is not yet the report not using template particles, organic solvent and emulsifying agent and preparing mesoporous polymer nanoparticle by means of only a step polyreaction.
Summary of the invention
The technical problem solved
In order to avoid the deficiencies in the prior art part, the present invention proposes the preparation method of a kind of mesoporous polymer nanoparticle.
Technical scheme
The preparation method of a kind of mesoporous polymer nanoparticle, it is characterised in that step is as follows:
Step 1: by styrene monomer, (methyl) vinylformic acid (ester) class monomer, control agent and water in mass ratio 20��80:20��80:0.1��5:500��10000 ratio stir formed mixed solution, mixed solution is heated to 50��90 DEG C;
Step 2: the mixed solution adding initiator and water again, at 50��90 DEG C of temperature, polyreaction obtains polymer nano-particle in 2��24 hours; In described mixed solution, the mass ratio of initiator and water is 0.1��5:20��200;
Step 3: remove unreacted monomer, control agent and initiator with water cleaning cleaning polyalcohol nanoparticle, obtain mesoporous polymer nanoparticle.
Described styrene monomer is vinylbenzene, 4-hydroxymethylstyrene or 4-1-chloro-4-methyl-benzene.
Described (methyl) vinylformic acid (ester) class monomer is vinylformic acid, methyl acrylate, ethyl propenoate, propyl acrylate, butyl acrylate, Hydroxyethyl acrylate, glycidyl acrylate, methacrylic acid, methyl methacrylate, ��-dimethyl-aminoethylmethacrylate, propyl methacrylate, butyl methacrylate, hydroxyethyl methylacrylate or glycidyl methacrylate.
Described control agent is 1,1-phenylbenzene ethene, 1,1,2-triphenylethylene, 1,1-dinaphthyl ethene or 1,1-phenyl napthyl ethene.
Described initiator is Potassium Persulphate, ammonium persulphate or Sodium Persulfate.
Useful effect
The preparation method of a kind of mesoporous polymer nanoparticle that the present invention proposes, be polymerized, by a step soap-free emulsion control, the polymer nano-particle obtaining and containing meso-hole structure by comonomers such as styrene monomer and (methyl) vinylformic acid (ester). This preparation method, without the need to adding template particles, pore-creating agent and emulsifying agent, only needs a step simple aggregation reaction. The meso-hole structure of polymer nano-particle can be found out clearly, and the specific surface area of mesoporous polymer nanoparticle is higher, even aperture distribution by photo.
Mesoporous polymer nanoparticle prepared by the present invention, has wide practical use in the carrier of atmosphere storage, parting material, medicine and biological active materials, catalysis and the field such as support of the catalyst, nano-reactor, photonic crystal, sensor.
Accompanying drawing explanation
Fig. 1: the transmission electron microscope photo of the mesoporous polymer nanoparticle of vinylbenzene and glycidyl methacrylate copolymerization
Fig. 2: the nitrogen adsorption desorption curve of the mesoporous polymer nanoparticle of vinylbenzene and glycidyl methacrylate copolymerization and graph of pore diameter distribution
Fig. 3: the transmission electron microscope photo of the mesoporous polymer nanoparticle of vinylbenzene and acrylic acid copolymer
Fig. 4: the nitrogen adsorption desorption curve of the mesoporous polymer nanoparticle of vinylbenzene and acrylic acid copolymer and graph of pore diameter distribution
Embodiment
Now in conjunction with the embodiments, the invention will be further described for accompanying drawing:
Embodiment 1: mesoporous polymer nanoparticle prepared by vinylbenzene and glycidyl methacrylate one step emulsifier-free emulsion polymerization
By 5g vinylbenzene, 5g glycidyl methacrylate, 0.05g1,1-phenylbenzene ethene, 100g water join in 250mL there-necked flask, in stirring at room temperature 30 minutes, add 0.05g ammonium persulphate, 20g water after being heated to 75 DEG C, react and obtain polymer nano-particle in 8 hours;With water abundant cleaning cleaning polyalcohol nanoparticle with the mesoporous polymer nanoparticle removing unreacted vinylbenzene, glycidyl methacrylate, 1,1-phenylbenzene ethene, ammonium persulphate vacuum-drying obtain vinylbenzene and glycidyl methacrylate copolymerization.
Embodiment 2: mesoporous polymer nanoparticle prepared by vinylbenzene and glycidyl methacrylate one step emulsifier-free emulsion polymerization
By 0.6g vinylbenzene, 2.4g glycidyl methacrylate, 0.03g1,1-phenylbenzene ethene, 80g water join in 250mL there-necked flask, in stirring at room temperature 5 minutes, add 0.05g ammonium persulphate, 20g water after being heated to 60 DEG C, react and obtain polymer nano-particle in 12 hours; With water abundant cleaning cleaning polyalcohol nanoparticle with the mesoporous polymer nanoparticle removing unreacted vinylbenzene, glycidyl methacrylate, 1,1-phenylbenzene ethene, ammonium persulphate vacuum-drying obtain vinylbenzene and glycidyl methacrylate copolymerization.
Embodiment 3: mesoporous polymer nanoparticle prepared by vinylbenzene and glycidyl methacrylate one step emulsifier-free emulsion polymerization
By 2g vinylbenzene, 3g glycidyl methacrylate, 0.05g1,1-phenylbenzene ethene, 80g water join in 250mL there-necked flask, in stirring at room temperature 10 minutes, add 0.05g Potassium Persulphate, 20g water after being heated to 80 DEG C, react and obtain polymer nano-particle in 6 hours; With water abundant cleaning cleaning polyalcohol nanoparticle with the mesoporous polymer nanoparticle removing unreacted vinylbenzene, glycidyl methacrylate, 1,1-phenylbenzene ethene, Potassium Persulphate vacuum-drying obtain vinylbenzene and glycidyl methacrylate copolymerization.
Embodiment 4: mesoporous polymer nanoparticle prepared by vinylbenzene and vinylformic acid one step emulsifier-free emulsion polymerization
2g vinylbenzene, 1.5g vinylformic acid, 0.03g1,1-phenyl napthyl ethene, 100g water are joined in 250mL there-necked flask, in stirring at room temperature 3 minutes, adds 0.1g Potassium Persulphate, 40g water after being heated to 80 DEG C, react and obtain polymer nano-particle in 6 hours; With water abundant cleaning cleaning polyalcohol nanoparticle with the mesoporous polymer nanoparticle removing unreacted vinylbenzene, vinylformic acid, 1,1-phenyl napthyl ethene, Potassium Persulphate vacuum-drying obtain vinylbenzene and acrylic acid copolymer.
Embodiment 5: mesoporous polymer nanoparticle prepared by vinylbenzene and vinylformic acid one step emulsifier-free emulsion polymerization
2g vinylbenzene, 1.5g vinylformic acid, 0.03g1,1-phenyl napthyl ethene, 100g water are joined in 250mL there-necked flask, in stirring at room temperature 3 minutes, adds 0.1g Potassium Persulphate, 40g water after being heated to 80 DEG C, react and obtain polymer nano-particle in 6 hours; With water abundant cleaning cleaning polyalcohol nanoparticle with the mesoporous polymer nanoparticle removing unreacted vinylbenzene, vinylformic acid, 1,1-phenyl napthyl ethene, Potassium Persulphate vacuum-drying obtain vinylbenzene and acrylic acid copolymer.
Embodiment 6: mesoporous polymer nanoparticle prepared by vinylbenzene and methacrylic acid one step emulsifier-free emulsion polymerization
4g vinylbenzene, 3g methacrylic acid, 0.02g1,1,2-triphenylethylene, 50g water are joined in 250mL there-necked flask, in stirring at room temperature 3 minutes, adds 0.05g Sodium Persulfate, 10g water after being heated to 75 DEG C, react and obtain polymer nano-particle in 24 hours; With water abundant cleaning cleaning polyalcohol nanoparticle with the mesoporous polymer nanoparticle removing unreacted vinylbenzene, methacrylic acid, 1,1,2-triphenylethylene, Sodium Persulfate vacuum-drying obtain vinylbenzene and methacrylic acid copolymerization.
Embodiment 7: mesoporous polymer nanoparticle prepared by vinylbenzene and hydroxyethyl methylacrylate one step emulsifier-free emulsion polymerization
By 2g vinylbenzene, 3g hydroxyethyl methylacrylate, 0.05g1,1 ,-phenylbenzene ethene, 100g water joined in 250mL there-necked flask, in stirring at room temperature 15 minutes, add 0.05g Sodium Persulfate, 15g water after being heated to 80 DEG C, react and obtain polymer nano-particle in 24 hours;With water abundant cleaning cleaning polyalcohol nanoparticle to remove unreacted vinylbenzene, hydroxyethyl methylacrylate, 1,1 ,-phenylbenzene ethene, Sodium Persulfate vacuum-drying obtain the mesoporous polymer nanoparticle of vinylbenzene and hydroxyethyl methylacrylate copolymerization.
Mesoporous polymer nanoparticle prepared by embodiment 8:4-hydroxymethylstyrene and Hydroxyethyl acrylate one step emulsifier-free emulsion polymerization
By 2g4-hydroxymethylstyrene, 3g Hydroxyethyl acrylate, 0.05g1,1 ,-phenylbenzene ethene, 100g water joined in 250mL there-necked flask, in stirring at room temperature 15 minutes, add 0.05g ammonium persulphate, 15g water after being heated to 80 DEG C, react and obtain polymer nano-particle in 24 hours; With water abundant cleaning cleaning polyalcohol nanoparticle to remove unreacted 4-hydroxymethylstyrene, Hydroxyethyl acrylate, 1,1 ,-phenylbenzene ethene, ammonium persulphate vacuum-drying obtain the mesoporous polymer nanoparticle of 4-hydroxymethylstyrene and Hydroxyethyl acrylate copolymerization.
Embodiment 9: mesoporous polymer nanoparticle prepared by vinylbenzene and methyl acrylate one step emulsifier-free emulsion polymerization
By 4g vinylbenzene, 2.5g methyl acrylate, 0.03g1,1 ,-phenylbenzene ethene, 90g water join in 250mL there-necked flask, in stirring at room temperature 15 minutes, add 0.05g ammonium persulphate, 15g water, react and obtain polymer nano-particle in 18 hours after being heated to 60 DEG C; With water abundant cleaning cleaning polyalcohol nanoparticle to remove unreacted vinylbenzene, methyl acrylate, 1,1 ,-phenylbenzene ethene, ammonium persulphate vacuum-drying obtain the mesoporous polymer nanoparticle of vinylbenzene and methyl acrylate copoly.
Claims (5)
1. the preparation method of a mesoporous polymer nanoparticle, it is characterised in that step is as follows:
Step 1: by styrene monomer, (methyl) vinylformic acid (ester) class monomer, control agent and water in mass ratio 20��80:20��80:0.1��5:500��10000 ratio stir formed mixed solution, mixed solution is heated to 50��90 DEG C;
Step 2: the mixed solution adding initiator and water again, at 50��90 DEG C of temperature, polyreaction obtains polymer nano-particle in 2��24 hours; In described mixed solution, the mass ratio of initiator and water is 0.1��5:20��200;
Step 3: remove unreacted monomer, control agent and initiator with water cleaning cleaning polyalcohol nanoparticle, obtain mesoporous polymer nanoparticle.
2. the preparation method of mesoporous polymer nanoparticle according to claim 1, it is characterised in that: described styrene monomer is vinylbenzene, 4-hydroxymethylstyrene or 4-1-chloro-4-methyl-benzene.
3. the preparation method of mesoporous polymer nanoparticle according to claim 1, it is characterised in that: described (methyl) vinylformic acid (ester) class monomer is vinylformic acid, methyl acrylate, ethyl propenoate, propyl acrylate, butyl acrylate, Hydroxyethyl acrylate, glycidyl acrylate, methacrylic acid, methyl methacrylate, ��-dimethyl-aminoethylmethacrylate, propyl methacrylate, butyl methacrylate, hydroxyethyl methylacrylate or glycidyl methacrylate.
4. the preparation method of mesoporous polymer nanoparticle according to claim 1, it is characterised in that: described control agent is 1,1-phenylbenzene ethene, 1,1,2-triphenylethylene, 1,1-dinaphthyl ethene or 1,1-phenyl napthyl ethene.
5. the preparation method of mesoporous polymer nanoparticle according to claim 1, it is characterised in that: described initiator is Potassium Persulphate, ammonium persulphate or Sodium Persulfate.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106632827A (en) * | 2016-09-28 | 2017-05-10 | 西北工业大学 | Preparation method of water-soluble amphiphilic polymer with functions of initiating and surface activity |
| CN107522813A (en) * | 2017-08-04 | 2017-12-29 | 西北工业大学 | A kind of preparation method of the pore polymer microsphere of multistage containing living polymerization sites |
| CN115252822A (en) * | 2022-08-29 | 2022-11-01 | 新乡医学院 | Preparation method and application of nano-drug particles for treating tumors by carbon free radical and immune regulation cooperation |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106632827A (en) * | 2016-09-28 | 2017-05-10 | 西北工业大学 | Preparation method of water-soluble amphiphilic polymer with functions of initiating and surface activity |
| CN106632827B (en) * | 2016-09-28 | 2019-04-05 | 西北工业大学 | A kind of preparation method of the water-soluble amphiphilic macromolecule with initiation and surface active function |
| CN107522813A (en) * | 2017-08-04 | 2017-12-29 | 西北工业大学 | A kind of preparation method of the pore polymer microsphere of multistage containing living polymerization sites |
| CN107522813B (en) * | 2017-08-04 | 2020-04-21 | 西北工业大学 | Preparation method of hierarchical porous polymer microspheres containing active polymerization sites |
| CN115252822A (en) * | 2022-08-29 | 2022-11-01 | 新乡医学院 | Preparation method and application of nano-drug particles for treating tumors by carbon free radical and immune regulation cooperation |
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Application publication date: 20160608 |